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ChemicalBook CAS DataBase List 2,7-DIBROMO-9H-CARBAZOLE
136630-39-2

2,7-DIBROMO-9H-CARBAZOLE synthesis

11synthesis methods
-

Yield:136630-39-2 82.5%

Reaction Conditions:

with triphenylphosphine in 1,2-dichloro-benzene at 180; for 3 h;

Steps:

6.3.6 2,7-Dibromo-9H-carbazole (11)

A solution of compound 10 (24.13g, 67.54mmol) and PPh3 (44.27g, 168.88mmol) in o-dichlorobenzene (120mL) was stirred at 180°C for 3h. After cooled down to r.t., the reaction mixture was purified by column chromatography on silica gel using dichloromethane-hexane (1:5) as the eluent to give the final purified product as white-off solids with yield of 82.5% (18.09g). 1H NMR (300MHz, (CD3)2SO) δ: 11.55 (s, 1H, -NH), 8.13-8.10 (d, J=8.4Hz, 2H, H5), 7.75-7.74 (d, J=1.5Hz, 2H, H2), 7.37-7.34 (dd, J1=8.4Hz, J2=1.8Hz, 2H, H4); 13C NMR (75MHz, (CD3)2SO) δ: 141.74 (C1), 123.05 (C4), 122.89 (C5), 121.95 (C6), 119.66 (C3), 114.81 (C2); HRMS-EI (m/z): [M]+ calcd for C12H7Br2N, 322.8945; found 322.8938 [(79Br) (79Br)M]+, 324.8950 [(79Br) (81Br)M]+, 326.8954 [(81Br) (81Br)M]+.

References:

Lin, Tzu-Chau;Chien, Wei;Dai, Shu-Wen;Lin, Hao-Wu;Liu, Yueh-Ching [Dyes and Pigments,2019,vol. 168,p. 140 - 150]

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